(Z)-2-(2-amino-thiazol-4-yl)-2-trityloxyimino-acetic acid-benzotriazol-1-yl ester | 128438-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (Z)-2-(2-amino-thiazol-4-yl)-2-trityloxyimino-acetic acid-benzotriazol-1-yl ester
• 英文别名: (Z)-(2-amino-thiazol-4-yl)-trityloxyimino-acetic acid benzotriazol-1-yl ester；(Z)-(2-aminothiazol-4-yl)-trityloxyimino-acetic acid 1-benzotriazolyl ester；Benzotriazol-1-yl (Z)-((Z)-2-Aminothiazol-4-yl)-2-trityloxyiminoacetate；2-(2-aminothiazol-4-yl)-(Z)-2-trityloxyimino-acetic acid 1-benzotriazole ester；benzotriazol-1-yl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-trityloxyiminoacetate
• CAS: 128438-02-8
• 化学式: C₃₀H₂₂N₆O₃S
• 分子量: 546.609
• InChiKey: NNXHTALPYXRANA-YLHCSOALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (Z)-2-(2-amino-thiazol-4-yl)-2-trityloxyimino-acetic acid-benzotriazol-1-yl ester 在 甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.25h， 生成 (6R,7R)-7-[(Z)-2-(Amino-thiazol-4-yl)-2-hydroxyimino-acetylamino]-8-oxo-3-[(Z)-2-oxo-1-phenyl-azetidin-3-ylidenemethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of (Lactamylvinyl)cephalosporins Exhibiting Activity against Staphylococci, Pneumococci, and Enterococci

  摘要：

  The synthesis and structure-activity relationships of a new class of vinylcephalosporins substituted with a lactamyl residue (1) are described. These compounds show excellent activity against enterococci and retain the broad spectrum activity of third-generation cephalosporins such as ceftriaxone.

  DOI：

  10.1021/jm950886v
• 作为产物：
  描述：

  头孢地尼侧链酸 、 1-羟基苯并三唑一水物 以100%的产率得到
  参考文献：
  名称：

  KAMACHI, HAJIME;OKITA, TAKAAKI;OKUYAMA, SATSUKI;NAITO, TAKAYUKI

  摘要：

  DOI：

文献信息

• Cephalosporin derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05804577A1

  公开（公告）日：1998-09-08

  The present invention relates to compounds of formula I ##STR1## wherein R.sup.1 is a group selected from 2-, 3-, and 4-hydroxyphenyl, 3-nitrophenyl, and 3-fluoro-4-hydroxyphenyl; as well as readily hydroyzable esters thereof, pharmaceutically acceptable salts of said compounds and hydrates of the compounds of formula I and of their esters and salts.

  本发明涉及公式I的化合物，其中R.sup.1是从2-、3-和4-羟基苯基、3-硝基苯基和3-氟-4-羟基苯基中选择的基团；以及这些化合物的易水解酯、药学上可接受的盐以及公式I化合物及其酯和盐的水合物。
• Orally active cephalosporins: synthesis, structure–activity relationships and oral absorption of 3-[( E ) and ( Z )-2-Substituted vinyl]-cephalosporins
  作者：Hirofumi Yamamoto、Takeshi Terasawa、Ayako Ohki、Fumiyuki Shirai、Kohji Kawabata、Kazuo Sakane、Satoru Matsumoto、Yoshimi Matsumoto、Shuichi Tawara

  DOI：10.1016/s0968-0896(99)00257-6

  日期：2000.1

  7beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamid o]-3-[(E)- and (Z)-2-substituted vinyl]-3-cephem-4-carboxylic acids was designed and synthesized using palladium-catalyzed coupling reactions of a 3-methanesulfonyloxy-3-cephem and an E substituted vinyl stannane or Wittig reaction of a 3-triphenylphosphoniummethyl cephem and an aldehyde as a key step. These compounds were evaluated for in vitro antibacterial

  一系列7β-[（Z）-2-（2-氨基噻唑-4-基）-2-羟基亚氨基乙酰胺基o] -3-[（E）-和（Z）-2-取代的乙烯基] -3- Cephem-使用3-甲磺酰氧基-3-cephem的钯催化偶联反应和E取代的乙烯基锡烷的钯催化偶联反应或3-triphenylphosphoniummethyl cephem和醛的Wittig反应设计和合成4-羧酸是关键步骤。评价这些化合物在大鼠中的体外抗菌活性和口服吸收。他们中的许多人对革兰氏阳性和革兰氏阴性细菌（包括流感嗜血杆菌）均表现出出色的抗菌活性。其中，FR86524（2j）。在C-3位置具有（Z）-2-（3-吡啶基）乙烯基部分的化合物具有最佳平衡的活性。尽管FR86254口服吸收率低，
• Derivatives of 3-pyrrolidylidene-2-one-cephalsporines
  申请人：Hoffmann-La Roche Inc.

  公开号：US05925632A1

  公开（公告）日：1999-07-20

  Compounds of formula (I) ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, aralkyl, cycloalkyl, R.sup.3 CO-- or --C(R.sup.4 R.sup.5)CO.sub.2 R.sup.6 ; where R.sup.4 and R.sup.5 are each independently hydrogen or lower alkyl, or R.sup.4 and R.sup.5 taken together with the carbon atom to which they are attached form a cycloalkyl group; R.sup.3 is hydrogen or lower alkyl and R.sup.6 is hydrogen, lower alkyl, lower alkenyl or a carboxylic acid protecting group; R.sup.2 is isobutyl, 2,2-dimethyl-propyl or cyclohexyl-methyl; n is 0, 1 or 2; X is CH or N; as well as readily hydrolyzable esters thereof, pharmaceutically acceptable salts of said compounds and hydrates of the compounds of formula I and of their esters and salts are disclosed. These compounds have valuable antibacterial activity.

  化合物的化学式（I）##STR1##其中R.sup.1是氢、较低的烷基、芳基烷基、环烷基、R.sup.3 CO-或-C(R.sup.4 R.sup.5)CO.sub.2 R.sup.6；其中R.sup.4和R.sup.5各自独立地是氢或较低的烷基，或R.sup.4和R.sup.5与它们连接的碳原子一起形成环烷基基团；R.sup.3是氢或较低的烷基，R.sup.6是氢、较低的烷基、较低的烯基或羧酸保护基；R.sup.2是异丁基、2,2-二甲基丙基或环己基甲基；n为0、1或2；X为CH或N；以及它们的容易水解酯、所述化合物的药用盐以及化学式I和它们的酯和盐的水合物。这些化合物具有有价值的抗菌活性。
• 1-carba-(dethia)-cephalosporin derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05939410A1

  公开（公告）日：1999-08-17

  Compounds of formula I wherein R.sup.1 is hydrogen, lower alkyl which is unsubstituted or substituted by fluoro, aralkyl, cycloalkyl, --COR.sup.4 or --C(R.sup.5 R.sup.6)CO.sub.2 R.sup.7 --C(R.sup.5 R.sup.6)CONHR.sup.7 ; where R.sup.5 and R.sup.6 are each independently hydrogen or lower alkyl, or R.sup.5 and R.sup.6 taken together form a cycloalkyl group; R.sup.4 is hydrogen or lower alkyl and R.sup.7 is hydrogen, lower alkyl, lower alkenyl or a carboxylic acid protecting group; R.sup.2 is hydrogen, hydroxy, lower alkyl-Q.sub.m, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aralkyl-Q.sub.m, aryl-Q.sub.m, aryloxy, aralkoxy, a heterocyclic ring or heterocyclyl lower alkyl, the lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aralkyl, aryl, aryloxy, aralkoxy and the heterocyclic ring being unsubstituted or substituted with at least one group selected from carboxy, amino, nitro, cyano, lower alkyl which is unsubstituted or substituted by fluoro, lower alkoxy, hydroxy, halogen, --COR.sup.6, --C(R.sup.5 R.sup.6)CO.sub.2 R.sup.7, --C(R.sup.5 R.sup.6)CONR.sup.5 R.sup.8, --CONR.sup.5 R.sup.6, --N(R.sup.6)COOR.sup.10, R.sup.6 OCO-- or R.sup.6 COO-- where R.sup.5 and R.sup.6 are hydrogen or lower alkyl; R.sup.7 is hydrogen, lower alkyl, lower alkenyl or a carboxylic acid protecting group; R.sup.8 is hydrogen, lower alkyl or phenyl which is unsubstituted or substituted with at least one halogen, hydroxy, amino, lower alkyl, or lower alkoxy; R.sup.10 is lower alkyl, lower alkenyl or a carboxylic acid protecting group; Q is --CHR--, --CO-- or --SO.sub.2 --; R is hydrogen or lower alkyl; R.sup.3 is hydroxy, --O--, lower alkoxy, --OM and M represents an alkali metal; m is 0 or 1; n is 0, 1 or 2; x is CH or N as well as readily hydrolysable esters thereof, pharmaceutically acceptable salts of said compounds and hydrates of the compounds of formula I and of their esters and salts are provided. These compounds have valuable antiinfective properties.

  提供公式I的化合物，其中R.sup.1是氢、未经氟取代或经氟取代的低烷基、芳基烷基、环烷基、--COR.sup.4或--C（R.sup.5R.sup.6）CO.sub.2R.sup.7--C（R.sup.5R.sup.6）CONHR.sup.7；其中R.sup.5和R.sup.6各自独立地是氢或低烷基，或R.sup.5和R.sup.6共同形成环烷基；R.sup.4是氢或低烷基，R.sup.7是氢、低烷基、低烯基或羧酸保护基；R.sup.2是氢、羟基、低烷基-Q.sub.m、环烷基、低烷氧基、低烯基、环烷烯基、低炔基、芳基烷基-Q.sub.m、芳基-Q.sub.m、芳氧基、芳基烷氧基、杂环环或杂环基低烷基，其中低烷基、环烷基、低烷氧基、低烯基、环烷烯基、低炔基、芳基烷基、芳基、芳氧基、芳基烷氧基和杂环环未经取代或经至少选择一个羧酸、氨基、硝基、氰基、未经氟取代或经氟取代的低烷基、低烷氧基、羟基、卤素、--COR.sup.6、--C（R.sup.5R.sup.6）CO.sub.2R.sup.7、--C（R.sup.5R.sup.6）CONR.sup.5R.sup.8、--CONR.sup.5R.sup.6、--N（R.sup.6）COOR.sup.10、R.sup.6OCO-或R.sup.6COO-的取代基，其中R.sup.5和R.sup.6是氢或低烷基；R.sup.7是氢、低烷基、低烯基或羧酸保护基；R.sup.8是氢、低烷基或未经氟取代或经至少一个卤素、羟基、氨基、低烷基或低烷氧基取代的苯基；R.sup.10是低烷基、低烯基或羧酸保护基；Q是--CHR--、--CO--或--SO.sub.2--；R是氢或低烷基；R.sup.3是羟基、--O--、低烷氧基、--OM和M代表碱金属；m为0或1；n为0、1或2；x为CH或N，以及公式I的化合物的易水解酯、所述化合物的药学上可接受的盐以及公式I的化合物及其酯和盐的水合物。这些化合物具有有价值的抗感染性能。
• A process for preparing cephem prodrug esters
  申请人：Bristol-Myers Squibb Company

  公开号：EP0355821A2

  公开（公告）日：1990-02-28

  The invention relates to a process for the preparation of a physiologically hydrolyzable ester of formula I wherein R² is hydrogen, R³ is hydrogen or methyl, and R⁴ is a physiologically hydrolyzable ester group which comprises (1) providing an O-protected acid of Formula I wherein R⁴ is hydrogen and R² is an O-protecting group of the type commonly used in the synthesis of cephalosporin compounds, and R³ is as defined above; (2) introducing the said R⁴ physiologically hydrolyzable ester group; and (3) replacing said R² O-protecting group with hydrogen.

  本发明涉及一种制备式 I 生理可水解酯的工艺 其中 R² 是氢，R³ 是氢或甲基，R⁴ 是生理上可水解的酯基，包括 (1) 提供式 I 的 O-保护酸，其中 R⁴ 是氢，R² 是头孢菌素化合物合成中常用的 O-保护基团，R³ 如上定义； (2) 引入所述 R⁴ 生理上可水解的酯基；以及 (3) 用氢取代所述 R² O-保护基。